摘要
有机发光材料具有种类繁多、色彩丰富、色纯度高、可调性好等特点,在有机电致发光器件、有机激光器、太阳能电池及光学传感器等诸多领域中有广泛的应用前景。其中,有机电致发光器件自发光、亮度高、视角宽、对比度高、超薄、能耗低、响应速度快,满足了人们对高品质平板显示器的需求。卟啉是饱和的红色发光材料,色纯度高,近年来在电致发光领域倍受人们的瞩目。本论文在充分调研卟啉作为电致发光材料的研究历史和现状的基础上,设计合成了多种以卟啉为母体的新型有机电致发光材料,并初步研究了它们的性质,为红色发光材料的应用研究提供了实验和理论上的依据。主要研究内容如下：
(1)调研、总结了大量有关卟啉的文献,简要地描述了卟啉的结构特征,较详细地综述了卟啉在有机发光材料中的应用,着重地阐述了卟啉作为红光电致发光材料的研究现状,在此基础上提出了本论文的设计思想。
(2)通过Adler缩合、Vilsmeier甲酰化、Williamson取代反应、Wittig反应合成了基于多枝咔唑的卟啉衍生物G1、G2和G3。采用核磁共振氢谱、基质辅助激光解吸电离质谱(MALDI-TOF)对其结构进行了表征。研究了它们的紫外、荧光、热稳定性及电化学性质。研究结果表明：它们的主要吸收峰在420nm左右,且随着枝数的增加,吸收强度呈现1：2：3的关系；发射峰在660nm,属于饱和的红光材料,而且具有较好的热稳定性。这些化合物具有制备红光电致发光器件的潜能。根据紫外吸收尾带和氧化起始电位得到了HOMO和LUMO能级值,为制备电致发光器件提供了参考。
(3)利用水相和无溶剂的Aldol缩合、Michael加成反应等反应合成了环金属化配体,再通过Knoevenagel反应合成了一系列光功能的卟啉类化合物Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8和Y9。采用核磁共振氢谱、核磁共振碳谱和电喷雾质谱对其结构进行了表征。系统的研究了它们的线性光学性质,它们的紫外吸收位于350-700nm之间,最大吸收峰在410nm左右,吸收峰随着溶剂极性的变化没有明显的变化规律；它们的发射峰在650nm左右,属于饱和的红光材料。结合电化学测试,得到了它们的HOMO和LUMO能级值。同时还对它们进行了热重分析,热分解温度高达200℃,热稳定性良好。这些研究结果为下一步制备电致发光器件提供了实验依据。
(4)以对苯二乙腈为原料,通过Knoevenagel反应合成了一系列具有聚集态荧光增强效应(AIEE)的化合物,采用核磁对其结构进行了初步的表征。对该类化合物的合成探索,为类似的合成工作提供了参考。
With various kinds, rich color, high color purity and good adjustability, organic optoelectronic materials have a broad prospect of applications in organic light-emiting diodes (OLEDs), organic laser diode, organic solar cells, chemical sensors, and so on. Among them, organic light emitting diodes satisfy the people's eagerness to high quality flat-panel display owing to self-luminous, high-brightness, wide viewing angle, high eontrast, thinness, low power consumption and fast response time. As one of saturated red luminescence materials, porphyrins greatly atrracted people's attentions recently. On the basis of a large amount of literatures investigation, we have designed and synthesised several new-type porphyrin derivatives. And the properties were also studied preliminarily which provided an experimental and theoretical referrence to application research of red luminescence materials. The main research contents are elaborated as follows:
(1) We briefly described the structure characteristics of porphyrin, detailedly reviewed the applications of porphyrin in organic light-emitting materials, and discussed current research state of porphyrin as red light electroluminescent materials according to the literatures. Based on these, new concepts and design ideas for the dissertation hatched.
(2) Through Adler condensation, Vilsmeier, Williamson substitution reaction Witting reaction, porphyrin derivatives G1, G2, G3 containing multi-carbazoles were obtained based TPPps. All the complexes were characterized by 1H-NMR and matrix assisted laser dissorption ironization time of flight mass spectrometry (MALDI-TOF MS). The UV-Vis, fluorescence, TGA, CV properties were investigated. The major absorption peaks of these compouds were at around 420 nm. And the absorbtion intensity present 1:2:3 with the increase of branch number. Their emission peaks were at around 660 nm, which demonstrates they were saturated red materials. They also have good thermal stability. Therefore, They have a potential of preparing electroluminescent device. The HOMO and LUMO energy levels, which can provide reference for OLEDs, were obtained from electrochemical and UV-Vis spectrum.
(3) Cyclometalation organic ligands were synthesized by the solvent-free or an aqueous phase Aldol condensation and Michael addition. Through Knoevenagel reaction a series of compounds Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8、Y9 were obtained. And their structures were characterized using NMR and ESI-MS. Their optical properties were also investigated systematically. The absorptions of the compounds lie in 350-750 nm and the peaks of them are ca.410 nm. Their emission peaks were around 650nm. The absorption peaks have no apparent laws with the changes of polarity of the solvents as well as the emission peaks. The HOMO and LUMO energy levels were obtained from electrochemical and UV-Vis spectrum. Their thermal stabilities were also studied and the results showed they had good thermal stability.These results provid an experimental referrence to preparing of electroluminescent device..
(4) Through Knoevenagel reaction a series of compounds with aggregation induced fluorescence enhancement effect (AIEE) were synthesized based on p-Phenylenediacetonitrile. And their structures were characterized preliminarily by NMR. The synthesis exploration to this kind of compounds provides reference for similar work.
引文
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